Use of α-chlorinated N-(tert-butanesulfinyl)-imines in the synthesis of chiral aziridines
Use of α-chlorinated N-(tert-butanesulfinyl)-imines in the synthesis of chiral aziridines
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DOI：
10.1021/ol0611245
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发表时间：
2006-07-06
期刊：
影响因子：
5.2
通讯作者：
De Kimpe, Norbert
中科院分区：
文献类型：
--
作者：
Denolf, Bram;Mangelinckx, Sven;De Kimpe, Norbert
[图形]手性α-氯叔丁基磺基醛与格氏试剂有效地反应生成高非对映异构体过剩的β-氯-N-亚磺酰胺。后一类化合物通过一锅高产率反应或与碱分离处理后环合成相应的手性氮杂环丙烷。通过α-氯原子与镁的配位能力解释了新合成的β-氯亚磺酰胺的非对映选择性，导致了与通常观察到的非官能化N-亚磺酰亚胺相反的立体化学结果。
[GRAPHICS]Reaction of chiral alpha-chloro tert-butanesulfinyl aldimines with Grignard reagents efficiently afforded, beta-chloro N-sulfinamides in high diastereomeric excess. The latter compounds were cyclized toward the corresponding chiral aziridines in a high-yielding one-pot reaction or after separate treatment with base. The diastereoselectivity obtained in the newly synthesized, beta-chloro sulfinamides is explained via the coordinating ability of the alpha-chloro atom with magnesium resulting in the opposite stereochemical outcome as generally observed for nonfunctionalized N-sulfinyl imines.